How would you deal with the "wannabee baller" friend?

I have this friend who is the definition of gawdy(gaudy). He wears versace shirts, true religion jeans, and lacoste sneakers. He leases a new Benz every year or two. He always wants to eat at fancy restaurants and bars. But he is so SO CHEAP IT MAKES ME SO MAD. He won't tip (if I force him, he'll tip sub 10 percent), and whenever we go to fancy places he orders the cheapest thing and mooches off me. Then we go to the bar and he orders some doochy drink (martini...shaken not stirred...HE SAYS THAT) and then doesn't tip the bartender, who ends up treating me like dirt because of my association with him. I just want to know if you have any advice for helping my friend out, or even helping me out with dealing with him. EDIT: This thread has devolved (or evolved) into an epic saga of my many adventures with douchefriend. Here is a list of the stories posted so far (will add titles later): Post 9 (pg 1): Once a Thief Post 62 (pg 5): Clubbing Post 70 (pg 5): Douchefriend Visits post 93 (pg 7): Fresh as I Return post 97 is pretty funny (not mine): Ostrichenis post 120 (pg 8): Jessica Post 144 (pg 10): Douchefriend Bio Post 155 (pg 11): "Now She'll Want Me" Post 168 (pg 12): Another Night Post 197 (pg 14): Sex Life (Part 1) Post 214 (pg 15): Sex Life (Part 2) Post 259 (pg 18): The Origins of Douchefriend: The Curious Case of Mr. M’bubee Post 271 (pg 19): Memoirs of a Douchebag Post 312 (pg 21): The Edison (Part One) Post 331 (pg 23): The Edison (Part Two)

I've known him since 4th grade, but he's only recently started down the "poser doosh" path

Well, if you've known him for that long, just be blunt about it. Tell him flat out that he's a poser, comes off as a douche, and that you're embarrassed to be around him when he's acting that way. If he has fully formed frontal lobes, he should be able to take some constructive criticism.

Thing is, one time me and my other friend paid him cash for dinner (including tip) and he was to pay with his card and leave tip. He tells us to head to the car and he'd take care of it. I'm a bit suspicious so I tell my friend to go back and check how much he left for tip while I walked him to the car. Guess how much he left on the tip line:

Zero dollars.

He basically took me and my friends tip money and padded his own wallet with it. We essentially yelled at him for hours, telling him how pathetic he was for driving a benz and not being able to tip even a little bit (it wasn't even his own money for godsakes) and trying to cover it up on top of that. We thought that would straighten him out, but I guess it didn't.

Thing is, one time me and my other friend paid him cash for dinner (including tip) and he was to pay with his card and leave tip. He tells us to head to the car and he'd take care of it. I'm a bit suspicious so I tell my friend to go back and check how much he left for tip while I walked him to the car. Guess how much he left on the tip line:

Zero dollars.

He basically took me and my friends tip money and padded his own wallet with it. We essentially yelled at him for hours, telling him how pathetic he was for driving a benz and not being able to tip even a little bit (it wasn't even his own money for godsakes) and trying to cover it up on top of that. We thought that would straighten him out, but I guess it didn't.

That is ridiculous. Quit being friends with this guy. Whatever possible benefit you might have gained from his friendship is severely outweighed and negated by the level of his douche-baggery.

But what I'm really wondering is if there is a way to minimize the collateral damage his demeanor causes (on me).

Besides appearing perpetually apologetic, no, there is nothing you can do. People judge you by your company, and frankly I'm judging you for being friends with that dude.

Not only is his public imagine douchey, he has actually fucking stolen from you. What the fuck is the matter with you? Where is your self respect? You must be a decent enough guy to realize how worthless that prick is, yet you hang out with him? You need to raise your standards dude.

what age are we talking about here? if it's a recent development, then maybe something happened to the guy and he's just trying something out. In which case telling him he's acting like a douche should straighten it out. If that's just how he is, either accept him or move on.